


Ménage à Dean

by Destiel_Cockles



Series: Destiel ficlets/drabbles based on pics/gifs [6]
Category: Supernatural
Genre: Anal Sex, Blow Jobs, Dean/Cas/Past!Dean, Destiel - Freeform, Dirty Talk, Established Castiel/Dean Winchester, Explicit Sexual Content, Inspired by GIFs, M/M, NSFW GIF, Oral Sex, Rimming, Sex, Sexual Fantasy, Size Kink, Smut, Teenage Dean Winchester, Threesome, Threesome - M/M/M, Time Travel
Language: English
Status: Completed
Published: 2015-05-20
Updated: 2015-05-20
Packaged: 2018-03-31 12:10:09
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 10,054
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3977506
Author URL: https://archiveofourown.org/users/Destiel_Cockles/pseuds/Destiel_Cockles
Summary: <blockquote class="userstuff">
              <p>Dean is always talking Cas into making his crazy kinky fantasies come true. This time he wants Cas to take them back in time so they can have a threesome with Dean as a teenager.</p><p>**Contains a nsfw gif</p>
            </blockquote>





	Ménage à Dean

 

Castiel was once a servant of Heaven. A warrior. Fierce and absolute. He knew his mission and nothing could convince him to do otherwise. He did not let the trivial things that humans so easily let themselves be manipulated by crack through that exterior.

Until he met Dean Winchester.

Dean made him doubt his mission. Made him want to have free will. He made him feel things he never felt. Before Dean, Castiel had no emotions, no feelings. He only obeyed. But gradually Cas found that when he was with Dean he was happy. The more he got to know Dean the larger the range of emotions he felt. Not only doubt and anger toward Heaven, but he also felt love and lust towards Dean. Dean possess something unlike any other human Castiel has ever encountered.

At first it was his selflessness, his devotion to a thankless job and a brother who often times, even though unintentionally, let him down. Dean was also the most beautiful creature Castiel had ever laid eyes on. It didn’t take long for him to give into his desires, but then again is there any one in creation who could resist Dean Winchester?

Dean can always get his way. It is why he is such an excellent hunter. Not only can he get the job done by making people think he is anyone Dean wants them to believe he is, he can also use these skills to not only get free booze, get laid and even make enough hustling that he and his brother can not only travel the country without a playing job but live a comfortable enough life.

So naturally when Dean was telling Cas about another one of his fantasies, Castiel knew he was totally screwed and not just in the literal sense.

Not that Cas did not enjoy Dean’s fantasies, because he enjoyed them _a lot._ They were so sinfully arousing to hear, and not just because of Dean’s deep orgasmic voice but because they were so dirty and kinky and Cas was always happy to oblige.

Until Cas heard Dean’s latest fantasy.

“Aww, C’mon Cas! I figured you would love this. I mean…can you even imagine what that would be like?”

Cas is staring at the ceiling. He and Dean have just fulfilled one of Dean’s many fantasies and here he was trying to work Cas over again. It wasn’t really fair, when Dean fucked him Cas always had such an intense orgasm—sometimes  even to the point they render him unconscious-- he is always in a blissful state of ecstasy and Dean knows that is the best time to get him to agree to something.

Cas shakes his head and gives Dean a firm, _“NO.”_

“Is it because it’s a threesome? I mean…you’re not exactly going to be cheating on me.”

Cas feels Dean pulling on his shoulder, rolling him so he is now lying on his side facing his boyfriend. He traces a finger down Cas’s jaw and smiles seductively at him. He leans in and presses several soft sensual kisses to Cas’s lips and Cas can almost feel his façade cracking. He tries to remain strong but then Dean leans his forehead against his and Cas is staring into those intense emerald eyes.

To top it off Dean adds, “Pleeease, baby. I love you, and I know you’ll love it.”

Cas’s jaw clenches. Dean is trying to soften him up. Not just because he said he loves him, which Cas knew he did although it was rare for Dean to just throw it out there, but he called him “baby”, a sentiment normally reserved for his precious car. Cas takes a deep breath and shakes his head.

“It’s dangerous, Dean.”

“Cas, all I’m asking is you take us back to the late 90’s and have a threesome with my younger self. What could possibly go wrong? Don’t go all Ashton Kutcher on me and say I’ll Butterfly Effect everything because I already told you I won’t say a word about the future and you can even erase the memories out of the young version of me.”

“Dean, something _always_ goes wrong.”

“Cas, it’s just gonna be you and me…and me. A younger version of me...like, Twink!Dean. And if I do say so myself, I was really fucking hot back them too. I mean I wanted to have sex with me and here’s my chance to not only do that but also have an amazing threesome with younger me and my hot boyfriend. It’s a win win for everyone.”

“Dean you know that I only use my time traveling ability if absolutely necessary. By necessary I mean if it is vital in a hunt or to evade an evil threat or get a necessary weapon to kill such a threat and return it. Not so you can get off on some fantasy of fucking yourself. You do that all the time. Not only that, it takes a lot of my…as you call it mojo and it also is dangerous.”

“Jerking off is not the type of fucking myself I was referring to and…” Dean sighs and shifts closer to Cas, wrapping his arm tight around Cas. He kisses him heatedly then pulls back. “Fine, if you don’t want to, it’s okay.” Dean’s tongue slides up behind Cas’s ear. He shivers when he feels Dean’s teeth graze it. “I just thought it would be hot to watch your sexy ass fuck the younger version of me while I fuck you. Make a Cas sandwich with Dean on both sides. You pounding your big fat cock into a version of me that’s just about your size, while I pummel into you so hard it just makes you fuck harder into me. You can feel my big dick hitting your sweet spot while my ass tightens around yours and-”

“Fine! One time. One. We go straight there, no mention of the Apocalypse, Lucifer, angels, of anyone dying or anything that ever happened between then and now. Even if you think it will help bring back someone in the end it could result in you or your brother being dead. We only have sex once then we leave and I wipe the memory out of your younger self.”

Cas closes his eyes and sighs, not wanting to see Dean’s huge self-satisfied smirk of yet again getting an angel of the lord to give in and give him everything he desires. The only thing Cas can think of now is having sex with two Deans…it suddenly hits him that there will be _two_ Deans involved, meaning double the trouble, double the manipulation….but also double the pleasure.

Cas wonders how one man can be so irrespirable that he can get even the most inconvincible beings in existence to do crazy asinine things like travel back in time to have a threesome with his boyfriend and a younger version of his boyfriend. He opens his eyes and has his answer when he sees the look in Dean’s eye, a look Dean reserves only for him that melts his hypothetical heart and makes him want to do anything to keep that look there rather than the pain it has now replaced.

“Cas, you’re fucking awesome. And trust me you won’t regret it because even back then I was practically a sex god.”

“How is this even going to work? I know you and you would never just take someone’s word for it that you are you. Younger you will think you are some sort of supernatural creature.”

“First, let’s call him Twink!Dean, only because all of these _‘you’s_ are getting confusing. What I’m gonna do is tell him a few things only I would know. Trust me, I know how to talk to myself.”

“Exactly how young are you going to be?”

“I say we go back to like, 1998 or so. I’d be about nineteen.”

“Why then?”

“Doesn’t really matter when that much but I know a specific week where Sammy was on a school trip and our dad was a few states away hunting a wendigo. Let’s just say it was a very memorable week where I lived it up and there is just one day in that week where I wasn’t having some wild crazy sex…and….”

“And?”

Dean sighs and bites his lip, debating on telling Cas. He decides it will most likely seal the deal, even though he is going to sound like a major girl. “The next day I do a little experimenting and….I mess around with a guy and it’s the first time I don’t top and I just thought if we went back to the previous day…I could technically say you were my first.”

Dean can tell that the thought of having Dean first has convinced Cas that this is one fantasy he cannot pass up. After a very long hour of Castiel repeatedly stressing the importance of not saying anything about events of the future just in case for some reason he is unable to erase the memories before they come back, and also not to bring anything back or alter anything in any way they were finally ready to go.

“Remember Dean, absolutely do not-”

Dean sighs and rolls his eyes. “Yeah yeah yeah I know. You told me several thousand times. No telling him anything or taking anything can we please just go I’m so fucking horny I’m about to lose my damn mind.”

“I think you already have. Are you sure you want to have sex with me and your past self?”

“Fuck yes.”

Cas takes a deep breath, grabs Dean’s hand and chants a few Enochian words while completing the spell and suddenly they are hit with a rush of air then are instantly transported back to the exact day Dean had been describing.

They are in a small town just outside of Chicago at a motel Dean instantly recognizes as the motel he spent his first week alone at having endless sex while drinking and smoking so much weed he prays his young self isn’t too fucked up at the moment to really enjoy it but if memory serves him right he woke up feeling awesome after having sex with a certain extremely kinky older woman named Rhonda. Dean grins at the memory and figures past him has just gotten back to the motel and smoked a few joints, trying to plan what to do or rather who to do for that day.

Dean walks past the Impala and whistles. “Damn, she looks so young.” Dean ignores Cas rolling his eyes and pauses. “You know…I really need a new alternator for Baby back home. I mean that couldn’t possibly effect-”

 " _Dean,”_ Cas says through gritted teeth. “You do not touch anything on that damn car or we will fly back to 2015 so fast your head will spin. You must not take anything back with you. Not even a blade of grass.”

“How would a blade of grass cause a domino effect that would change the outcome of our future?”

Cas pinches the bridge of his nose and takes several long slow breaths. He still cannot believe he has agreed to this. “Just figure out where you are and don’t touch anything.”

“How are we supposed to have sex if I can’t-”

Cas pushes his forehead against Dean’s, looking into his eyes. “You know what I mean.”

“I know…I just wanna get you all riled up because, one, you’re even sexier when you’re pissed and two, you know I love it rough and I love getting you all hyped up. Hey, don’t take it easy on younger me just because he is not quite as muscular as I am now. Don’t hold back.”

Dean goes to the motel room in front of where the Impala was parked. Castiel went invisible, ready to intervene in case younger Dean thinks Dean is actually some sort of threat and is too quick for Dean or things get out of hand  if they get in a fight and Dean injures the teenager which could ultimately affect him presently.

Dean knocks on the door, he hears a soft gasp from Invisble!Cas when Twink!Dean answers the door. He is shirtless, wearing a pair of jeans slung low on his hips and is extremely sexy. He has six pack abs and large biceps but is nowhere near as muscular as Dean is now.

Twink!Dean is looking Dean up and down, not sure what the hell is going on but he can see the similarities. Dean knows himself and knows he has his hand on the gun in the waistband of his jeans.

“Who the hell are you?”

Dean grins, and his younger self narrows his eyes. “I’m you about fifteen years from now.”

Twink!Dean raises an eyebrow and slides his tongue over his full pink lips. Dean feels himself getting hard, it’s such a mind fuck to be aroused by himself but _damn_ , he really is a sex god because even just standing there Twink!Dean is making his older self want to shove him back against the wall and fuck his younger self so hard he can feel it when he gets back to his own time.

“Look, I know what you’re thinking and I’m not some kind of demon or shifter or anything like that. You need to listen to me.”

Twink!Dean leans against the doorframe and Dean feels the blood rushing to his quickly hardening cock as the younger version of himself smirks and his dimples push in.

 _Jesus fucking Christ, I’m so fucking hot_ , Dean thinks to himself. He feels a nudge and chuckles to himself, knowing Cas must have just read his mind. He realizes if he pays special attention to what about him is extra sexy he can use it to his advantage later with Cas

“Dude, I don’t have to do shit. You’ve got exactly five seconds to tell me what the hell you’re doing here before I knock your ass out, you really expect me to believe you’re from the future?”

Dean knows he is stubborn and not easily swayed so he blurts out. “I’m you and I have this way to travel in time and all I wanted to do was have a threesome with my boyfriend and my younger self,”

“Your boyfriend, huh? What’s he look like?”

Dean slides his tongue across his lips and smirks. He can tell Twink!Dean is thinking it over and he just happens to know that he had been thinking of trying to have a threesome that week since he was alone, and since he had several threesomes with girls already he was thinking of doing it with guys but was hesitant since he had always been a strict top but Dean knows once the  teenager realizes Dean really is an older version of himself they will be having hot sex. He prays that he is not as stubborn as he usually is because he is hornier than hell from looking at his gorgeous self but from the way the teenager is looking at him he is loving the idea of hooking up with an even more gorgeous more experienced version of himself.

“Dark hair, insanely hot, deep blue eyes…and I seem to remember wanting to have a threesome since Dad and Sammy are gone for a few more days.”

“You a mind reader or somethin’?”

“I told you, I’m you…ask me anything.”

He pulls his gun and points it at Dean, but steps to the side and nods for him to follow him. “You try anything I blow your head off, no matter how pretty it is,”

Twink!Dean winks at Dean and motions for him to sit down at the table.

“First off, I call the shots. Speaking of shots…”

Dean watches as Twink!Dean takes a bottle of holy water and pours some in a shot glass then sets it in front of him.

“Down that.”

Dean is impressed that he killed two birds with one stone, giving him the shot of holy water in a silver lined cup. Dean downs it and picks up some rock salt that is sitting on the table then rubs it against his skin.

“See? Now how about this…I just happen to know that last night you hooked up with the kinkiest woman you have ever met so far. Not only was Rhonda a smoking hot cougar but she also made you try something on that you thoroughly enjoyed.”

Dean sees his younger self blush slightly but quickly recover, the corner of his mouth twitching as he tries not to smile.

 Yeah? That’s pretty good…” He tries thinking of something to ask the man claiming to be a future version of himself. He looks like what Dean would expect himself to look like, he is glad to see he is still smoking hot and even more muscular. He looks a little tired but he knows that comes with the job, He is almost convinced when he names the one name Dean would never tell anyone about, and he especially would never ever mention the panties, noticing he didn’t actually say the word out loud because he refuses to even think the word but he has to be positive.

“If you’re me…Tell me something else only we would know, just so I can be sure you haven’t been spying on me or know a psychic or some shit.”

Dean tried thinking of something he would never have told anyone when he was a teenager but there really wasn’t too many secrets besides the Rhonda Hurley thing. Most of his secrets were sexual things and the only things he thought about he was reluctant to say with Cas listening.

Dean sighed and tried for something that would probably go over the angel’s head and he would have no idea what Dean was actually talking about but the teenage version of him would.

“We normally don’t like fucking around with girls that want us to take them on dates ever since we took twelve different girls to see Titanic hoping to get blowjobs but most of the time not only was the girl crying at the end of the movie you were tearing up too a couple times and it wasn’t just from crappy head.”

Dean noticed Twink!Dean’s jaw clench like he was pissed he even mentioned it and he could tell he was trying to come up with something good, but Dean was almost positive by the look in his eyes that he had him but knowing himself he would want to have the last word which could go on forever but being older and more mature he would let the boy have his way…that and he was so damn horny he was about to lose his mind.

While the teenager thought of another question Dean wondered how anyone could ever resist him, he was so fucking sexy even just sitting there, It was no wonder he practically had every girl and guy he had ever met begging him to have sex with them. It was one thing to look in the mirror and see his perfect reflection but to see it for real was even better, like HD. Dean felt a slap across the back of his head and grinned, Cas was obviously internally rolling his eyes at Dean thinking about how hot he is.

Twink!Dean took a long sip of whiskey then grinned as he slid the bottle over to Dean. “What’s the name of the girl we fucked on our 18th birthday?”

Dean took several long drinks as he thought it over. He had sex with more girls—and guys for that matter—than he would ever remember but there were a select few reserved in the spank bank for later. Dean knew he was hitting him with a trick question.

“Technically it was after midnight when we fucked her so it wasn’t actually on our birthday, but for the hell of it her name was Amy, super hot and kinky, and we banged her right after her twin brother who we all know wasn’t that impressive and have no idea what his name was because she just wanted to watch us fuck the boy version of her first.”

Twink!Dean nods. “Impressive. Okay…so tell me more about the current threesome you want to have…you said boyfriend, what’s up with that?”

"Look, I know what you’re thinking. I mean hell, you _are_ me. I lived the same life you have I just know more now. After a while hooking up with all these people…” Dean sighs and bites his lip, not sure how to word it in a way the teenage version of himself would understand. “I know I sound like a chick right now but I can’t put it in to words, you know we suck at that. But I guarantee you when you take one look at my boyfriend you’ll honestly think he fell straight from Heaven.”

Dean felt Cas nudge him and he chuckled. He was explicit about telling Dean not to ever mention he was an angel but he couldn’t resist making it sound like his favorite cheesy pick up line.

“One more thing, you’re gonna have to trust me on this. He’s not exactly human…well he is but he isn’t and I can’t tell you but I swear he’s one of the good guys and he saves our ass all the time.”

“What is he? He’s not like a vamp or werewolf or somethin’, is he?”

Dean shakes his head. “Nah, nothin’ like that…just, go with me on this when you find out…it’s really hot and…you just gotta meet him. I know you’re gonna love him. So you in or what?”

Twink!Dean takes another slow sip of whiskey then shrugs. “Ah, what the hell, can’t pass up some awesome sex. You’ve gotta be me, I mean you’re smoking hot and as long as your boyfriend is too…yeah, I’m in..”

“Awesome. I’ll be right back.”

Dean goes outside so he can pretend to get Cas since they agreed that they would not let him know about Cas’s powers. When Cas appears Dean can immediately tell by his facial expression he is getting pissed.

“Dean, I thought we agreed we would tell him I’m human.”

Dean shakes his head. “Won’t work. I know me, I felt something different about you, and I know he will to. He’s gonna know you’re not human and since like I said, I know me, if I just tell me like it is, then I won’t get pissed…and all this is giving me a headache so let’s get on to bigger and better things.”

Dean wraps his arms around Cas’s waist and pulls him into a kiss. “So, whaddaya think? I could practically hear you getting hard when he opened that door.”

Cas blushes and Dean grins as he leans in and kisses him again then pulls back, leaning his forehead against Cas’s while he laces his fingers with Cas’s and squeezes his hand.

“This is gonna be epic…I promise you won’t regret it.”

Cas nods, he knew it would be before he even laid eyes on the younger version of Dean but now that he has Cas wants it just as much as Dean does, maybe even more. Cas takes a deep breath and lets Dean pull him back into the motel room. He knows this is going to be some of the most epic sex he and Dean have ever had, how could it not be with two Deans…but there are two Deans, and one is a handful as it is and Cas has a feeling they will double team against him to talk him into a whole lot more than one threesome.

Dean opens the door and grins. “Dean… this is Cas.”

Twink!Dean walks over and Dean knows he is trying his best to keep his cool. After all, he’s Dean and that’s just the way he rolls. He can see him looking Cas up and down then he walks over to Dean and pats him on the shoulder.

“I see we haven’t lost our excellent taste. When you said boyfriend I was sure you were turning us into a giant douchey girl, but holy fucking shit…and you traveled back in time to let me hit that? You’re fucking awesome, man!”

“Well…actually I was thinking more along the lines of watching him fuck you then me fucking him into you as he fucks you into the mattress…but hey, round two is all up to you.”

Cas shoots Dean a loaded look but Dean grabs his ass and leans in, whispering, “You know damn well you can’t just have one.”

“I thought we had a strict policy?” Twink Dean asks, raising an eyebrow at his older self.

Cas tilts his head and scrunches his eyebrows together. Dean chuckles when he can clearly see that this gets to his younger self as much as it does to him presently. He knows Cas is trying to stay ahead of them but is lost when Dean knows what Twink!Dean is talking about before he even says it.

“I know, but trust me, once you bottom…the policy can change on occasion.”

“So how’re we gonna do this?” Twink!Dean asks.

Dean grabs Cas and kisses him passionately. As the kiss gets more intense Dean shoves him up against the wall, sliding his hand down Cas’s thigh then grabbing it and pulling it around his waist as he thrusts against him. Cas pulls back gasping for air a few minutes later.

“Damn, that was hot.”

“How ‘bout you show me how hot it is.”

Dean grins and steps to the side as Twink!Dean walks over. He grabs Cas’s tie and jerks him forward, crushing his lips to Cas’s. Cas seems hesitant at first so Dean encourages him.

“C’mon baby, it’s just like you’re kissing me, just a younger version.”

Dean chuckles when the teenager pushes Cas up against the wall, unbuttoning the stunned angel’s shirt while kissing him, his tongue ravaging around his mouth while he thrusts against him. Cas apparently thought that Dean would have been a little less aggressive when he was younger which is obviously not the case. Dean watches as his younger self practically rips Cas’s clothes off and chuckles to himself when Cas looks surprised. By now he would have thought that nothing about him would surprise Cas, he should have expected Twink!Dean to be feisty and sexual because if there is one thing Dean has never been shy about it’s sex.

Dean plops down on a chair while he watches Twink!Dean shove his jeans and boxers down then practically drag Cas over to the bed. He glances up at Dean and slides his tongue across his lips.

“So are there any rules?”

“Do we ever have any?”

The teenager grins seductively at Dean then at Cas. “Goddamn I fucking love how awesome I am. Still can’t believe this but then again I am fucking awesome. Apparently my fantasies keep getting better as I get older. How old are you guys anyway?”

Cas glances at Dean nervously, not sure how to answer. “We’re from 2015.”

“Dude, you think I wanna do math right now? Actually, never mind it doesn’t matter. Did you guys bring anything?”

Dean reaches in his pocket and tosses a bottle on the bed. The teenager picks it up and raises an eyebrow. “Cherry flavored huh? So I guess you two get all kinds of kinky. This all you brought?”

“What? You want some dildos or vibrators or something? I’m sure there are some handcuffs or zip ties around here somewhere but I didn’t think I’d bring you to the red room of pain on the first date.” When both Cas and the teenager look at him like they have no idea what he is talking about Dean chuckles. “It’s a reference to…um, never mind just start with sex, geez a threesome isn’t kinky enough or what?”

“I meant condoms you smartass.”

Dean slid his tongue across his lips and smirked. “Better than being a dumbass. We don’t use rubbers.”

“Wait, how do I know you don’t have anything?”

“He’s clean. We’re the only ones who’ve ever gotten to tap that ass.”

“We the only one he’s ever done too?”

Dean nods. “Yep.”

“Damn that’s hot. So Cas belongs to us, huh? This is going to be fucking awesome!” Twink!Dean glances as his older self and grins then smiles seductively at Cas. “So…let’s fuck.”

The teenager shoves Cas back and lies over him, sucking down on his neck as his hand slides across Cas’s chest. He pulls back a few seconds later and looks at the angel.

“Damn you’re fucking shy. Bet you aren’t shy with him anymore. You seem like one of those closet kinky bastards.” He glances up at Dean and grins. “Am I right?”

“Well no one is quite as kinky as us…but yeah, once he gets all horny and desperate he’s kinky as hell.”

Twink!Dean grabs Cas’s shoulder and rolls them around so Cas is now on top of him. “How ‘bout since you guys came here to show me a good time I lay here and enjoy it.”

Cas gently slides a finger across Twink!Dean’s rim. As he is easing his finger into him Cas glances at Dean who is watching. Dean looks hornier than fuck, he’s sitting in an armchair with his legs splayed open rubbing the front of his jeans.

“Dean.”

“Yeah?” They both answer in sexed out voices at once.

“I mean…my Dean. Older Dean…I want you to take your clothes off while you watch.”

Dean kicks his shoes off as he pulls his shirt over his head then he shoves his jeans and boxers off. Cas watches as he begins slowly stoking his cock. When their eyes meet they stare into each other’s pupil blown eyes for several seconds.

Twink!Dean huffs impatiently. “You two gonna sit there and eye fuck each other all day or we gonna actually fuck?”

Dean grins as Cas shoves two fingers deep inside of the younger version of himself, his grin widening as he watches the look of pleasure on the boy’s face as he glances over at him.

“Damn I thought my cock was huge now but shit…I’d love to hear how loud you can make your boyfriend scream with that monster.”

“As soon as he starts making you scream I will.”

Cas has three fingers in Twink!Dean, his eyes darting back and forth between the older and younger version. His cock is so hard it’s painful from being around so much hot sexy Dean. One was hard enough to be around but two made him feel like he was going to explode.

“You gonna fuck me with your dick or just your fingers?”

Cas eases his pinky in under his fingers and pounds them in as the younger Dean pushes back hard. He hears Dean chuckle and glances up at him.

“Told you I’ve always been a bossy bottom.”

“C’mon Cas… _fuck_ , I’m so goddamn horny I’m about to shove you down and ride you.”

Cas eases his fingers out then pours more lube onto them and slides them back in. He hears him whimpering softly and scissors his fingers several times.

“Aw _fuck_ …” Twink Dean moans, sinking down on the bed as Cas’s fingers plunge in deeper.

“Fuck him Cas,” Dean says in a strained voice.

Cas looks at his Dean and sees he is wrecked just from watching Cas finger the younger version of himself. Cas can hardly wait to see what Dean looks like when he’s actually fucking him.

Cas teases his cock across Twink!Dean’s rim, pressing it against his tight entrance. He nearly forgot that this version of Dean has never been fucked and just the thought of being the first to split him open has precome sweating out of his cock.

When Dean pushes back Cas grabs his hips, his fingers pressing into them so hard there are already finger shaped bruises forming.

“C’mon…”

Cas pushes then head of his cock in, already meeting resistance. He circles his hips as he gradually works himself in further. As soon as he feels himself push past the ring of muscle that was holding him back he lets out a moan and starts thrusting. He feels the teenager pushing back so Cas starts pulling him into his thrusts, pausing a moment to savor the tight heat surrounding his cock. It is almost exactly like fucking his own version of Dean, the only difference being he is lighter and Cas doesn’t realize right away that he is pushing and pulling him even harder than normal.

“Son of a fucking bitch! Dude, you better fucking marry him because… _goddamn_ …”

Watching Cas fuck him is the hottest damn thing Dean has ever seen. He wonders why he didn’t bring a camera, or why he never recorded them before. Not that he would sit and watch it because he would much rather have the real thing but from this point of view he can not only see the hot faces Cas makes but also the ones he is making and watching is harder than Dean thought because even though he is enjoying this more than any porn ever he would much rather be joining in.

Cas glances over at Dean and groans, he watches him thrust into his fist as he watches his boyfriend fuck the younger version of himself. Cas wants Dean to fuck him bad, he can hardly imagine what it will feel like to fuck Dean while being fucked by another Dean. The thought almost makes him come.

“Dean, _please.”_

Luckily Dean knows exactly what Cas wants, he can tell by the way his voice is strained. Cas’s eyes are barely even blue, his pupils almost completely eclipsing the beautiful color. Dean jumps up then kneels on the bed behind Cas and kisses the back of his neck as he nudges his legs a little further apart. He slides a finger across Cas’s rim as he watches Cas fuck into the younger version of himself. He pushes Cas down so he is lying over the teenager as he continues to work him open. Twink!Dean catches his eye and smirks then quickly pushes himself back against the angel as Dean lies over him so Cas is pressed tightly between them. Cas groans as he feels himself plunge deep into the boy, so deep his balls are pressed tightly against his ass.

Dean takes this opportunity to start working Cas open. He leans down and runs his tongue across Cas’s rim, poking at his puckered hole. He presses his tongue against it then licks roughly around then pulls back and eases a finger into him. Once he has him worked up to two fingers he spreads him open and plunges his tongue deep inside, sliding it along the silky inner walls.

“Ah, fuck...Dean!”

Dean feels Cas’s rhythmic movements as he fucks into his younger self. He hears Twink!Dean cursing and making a litany of hot noises as Dean pulls back and pounds his fingers into Cas, quickly working another finger in because this is so damn hot and he’s way too horny to wait.

Cas feels Dean kneel up and hold him open. He slowly pulls out of the younger Dean and just as he is thrusting back in Dean thrusts into him hard and starts rocking his hips. They all moan as Dean starts fucking into Cas with hard powerful thrusts which makes Cas thrust into Twink!Dean even harder.

Dean can feel Cas shuddering with pleasure as he grabs onto his hips and thrusts faster, forcing the angel to pound in harder and hearing just how hot he sounds while Cas is fucking him is turning him on a hell of a lot more than he thought it would.

Dean pulls out and Cas glances over his shoulder and whimpers. Dean leans down and kisses him then grins.

“Were gonna reposition. Get up.”

Cas eases out of Twink!Dean, expecting him to object but he is watching the older version of himself and must be able to tell he has an even better idea and he obviously knows just how dirty of a mind he has and trusts that this will be worth it. Dean pulls Cas off of the bed and the teenager gets up too. Dean lays down and grins.

“Cas, you ride me while you fuck him and he can fuck my face.”

Twink!Dean grins widely then gives Dean a skeptically look. “You sure you wanna do that? I mean…”

“’Like you don’t want to know what our lips feel like.”

“True…wait, but that means I’m gonna have to blow you right?”

“You know we’ve got cocksucker lips.” 

“If you were anyone else I would punch you right now.”

“Then you’d be punching yourself.”

Twink!Dean rolls his eyes. “Yeah, we’re too pretty and I don’t want to do some serious damage that might affect me when I’m older since we’re such badasses too.”

Cas sighs impatiently. “Are you two going to talk about how immaculate you are all night or are we going to actually do something besides bask in your awesomeness?”

Dean smirks and winks at his younger self. “He’s right, it would take centuries to describe our awesomeness.”

Dean grabs Cas’s arm and pulls him onto the bed. Cas straddles Dean, sinking down on his cock. Dean glances at the teenager and gestures for him to climb onto the bed, but he sits down in the chair Dean was sitting in.

“First I wanna watch you two go at it a little. I’ve never had a live porno before. Now with two guys anyway. Plus it couldn’t hurt to learn a few pointers…not that I need them, we’re sex gods, right?”

Dean chuckles under his breath when he sees Cas roll his eyes. He figures he’ll give his younger self a good show, even though he sadly will not remember any of it. Dean shoves Cas onto his back, immediately thrusting in him with hard powerful thrusts. He pulls one of Cas’s legs over his shoulder and starts pummeling into him so hard the bed is smacking against the wall and the bed is creaking. Cas’s eyes slam shut and he groans loudly. Dean grins and slowly pulls out then teases his cock across Cas’s rim.

“You love my big fat dick, don’t you?”

Cas nods, pushing down in an attempt to get Dean to stop teasing him. When he whimpers softly Dean pushes the head of his cock in then eases it back out.

“Tell me how bad you want it, how desperate you are for my cock.”

 _“Please_ , Dean…”

“Say it.”

“I want your big fat cock in me.”

Dean grins and pulls Cas’s other leg over his shoulder then slams into him hard. Cas’s back arches up and he yells out Dean’s name. Dean glances at Twink!Dean and his grin widens when he sees his hand furiously pumping up and down his cock in rhythm with Dean’s thrusts.

“You want in on this yet?”

The teenager jumps up as Dean lays back, bring Cas with him so he is once again straddling his hips. He climbs on the bed then glances down at Dean for guidance.

“C’mon, we’ve never been shy in bed. Don’t start now. Just straddle my chest and lean forward a little so he can get back in your tight little ass then I’ll start deep throating you.”

Dean stops thrusting into Cas long enough for them to get settled. He pulls the teenager a little closer then thrusts into Cas to get him to start going. Dean sits up enough so he can reach him and pauses.

“Always wondered how the hell anyone could deep throat us… _shit_ we’ve got a big dick.”

Dean catches Cas’s eye and smirks when the angel rolls his eyes then starts slamming into the younger Dean, impaling himself down on Dean’s cock harder with each thrust. The teenager’s mouth falls open in silent ecstasy, his eyes slamming shut. Dean wraps his fist around his thick cock, jerking and twisting his fist exactly the way he likes it, brushing his finger across the head on every upstroke. When he glances back up at Cas he notices he is still holding on to the boy’s hips, normally by now Cas is getting more grabby since the hornier he gets the more he cannot keep his hands off of Dean.

“Don’t be afraid to touch him Cas…it’s still me. Don’t be shy.”

Cas tentatively wraps an arm around the teenager and slides a hand across his chest. He is not quite as thick as his Dean but still very muscular and only slightly smaller. He is a lot closer to Cas’s size though and Cas seems to get into it right away, immediately tweaking the boy’s nipples to try and get to him like he knows it will.

Twink!Dean is breathing heavily, he has Cas fucking into him hard while pinching his nipples and sucking on his neck as Dean teases his tongue across the head of his cock. When the teenager reaches down and curls his fingers through Dean’s hair and pushes down, Dean starts sucking down on the head, swirling his tongue around as he thrusts up into Cas hard. Dean moans as he feels Cas clenching down on him hard. He starts bobbing his head up and down as he hollow out his cheeks.

“ _Fuck!”_ Twink!Dean yells out, his entire body shuddering as Cas’s dick slams into his prostate. Cas shifts and continues to hammer into his sweet spot while bouncing around on Dean’s cock hard. When he feels Dean continually hammer into his prostate he leans forwards and starts sucking down  harder on the teenager’s neck, making a trail of bruises on each side.

Dean glances up at the younger version of himself and groans at how gorgeous he looks. His teeth are tearing into his full luscious lips which have nearly doubled in size. When his eyes open and Dean stares into the green eyes that are so pupil blown his eyes almost appear black he moans and feels the cock in his mouth twitch hard.

“Goddamn this is… _fuck!_ Fucking incredible. We’re so fucking awesome, dude. I-”

The teenager’s voice cuts out and his mouth falls open in a silent scream as the sensation of his dick stretching out Dean’s throat and Cas hitting his prostate at once becomes too much. He starts coming  as he is almost thrown into an ecstasy coma.

Dean swallows down the come, deep throating his dick as he groans because he thinks he tastes fucking incredible. He starts thrusting into Cas hard because Cas is clenching down on him hard because he is currently coming into the younger Dean’s ass which is clamped down on his cock like a vice. Cas circles his hips and feels Dean start to come and they both grind and hump into each other while Cas tightens his arms around Twink!Dean who has gone completely boneless in his arms.

Dean pulls off as Cas slowly eases out of the teenager and sets him next to Dean. Cas spoons him from behind, slowly running his fingers down the teenager’s back. His eyes close and he moans, his body tingling from all the stimulation.

“That was so fucking awesome,” Twink!Dean whispers.

“I want to watch you two make out,” Cas says to Dean.

Dean leans in and kisses the teenage version of himself which even though it is a total mind fuck it is mind blowing because he cannot get over how amazing it feels. He always knew he’s the best kisser ever but to actually feel it, especially when Twink!Dean regains a few more brain cells and gets into it because then it gets so intense they are suddenly all over each other. Dean thinks to himself how he really is a sex god and hears Cas sigh. He knows Cas is reading his mind and sends him a message that he wants to fuck himself so he can literally say he has fucked himself and glances at Cas.

Cas raises an eyebrow and Dean mentally adds they can do anything Cas wants if he lets the teenage version of him fuck Cas while Dean fucks him. Cas nods and Dean pulls back and teases his cock against the boy’s rim.

Dean grunts as he slips the head of his cock in and meets resistance. “So fucking tight! Goddamn son of a bitch I have an amazing ass.”

“And an amazing cock,” adds Twink!Dean.

Cas makes an impatient noise and nudges Dean, already tired of hearing the Deans complement themselves. “Fuck him while I watch.”

Dean shoves the boy’s thighs up and thrusts in hard. He glares up at Dean and Dean can’t help but think how sex he looks when he’s pissed.

“Yes Dean, you are always hot and sex. You are literally the sexiest thing in existence so get over it.”

Dean shoots Cas a loaded look to remind him that the younger version does not know what he is or that he cannot read minds but the teenager is pissed so he is barely paying attention.

“Watch it, you’ve got a huge fucking cock and you’re ramming it in…us…me. Whatever. Give me a fucking minute, Jesus fucking Christ.”

Dean chuckles, he hasn’t been able to say certain words since he began fucking an angel of the Lord so every time his younger self says goddamn or things to that effect he can practically hear Cas cringing at the blasphemy.

Dean mutters an apology then slowly circles his hips. As soon as the teenager starts pushing down for more Dean shoves his thighs up so far he is practically bending him in half and starts pummeling into him.

“Oh, _fuck!_ Holy fucking _shit!”_

“Yeah, you like feeling that big dick stretch that tight virgin ass out don’t you?”

“Your boyfriend got that honor,” Twink!Dean retorts with a moan.

Cas sits back, completely amused because he does love listening to Dean talk dirty but it is even better because they seem to be trying to outdo the other, which he should have expected since Dean is the most competitive person on the planet in addition to being the hottest. It is almost too much sexiness to handle and wonders if he can get a future version of Dean in on the action but decides it would probably make the universe implode on itself to have so much pure sex in one room at one time.

Dean is pounding into Twink!Dean’s prostate, loving how incredibly tight his ass is and how much he is turned on by how sexy he looks.

“We’re getting mirrors on the ceiling,” Dean smirks at Cas and grins then adds, “How ‘bout you mount him so I can watch how hot it is to fuck you while you get fucked by me at the same time.”

Cas straddles the younger Dean but his Dean maneuvers around so he is facing the younger one. Dean leans in and sucks down on his neck and whispers, “I wanna watch your gorgeous ass take him in.”

Dean slows down as Cas sinks down onto Twink!Dean’s cock and they all moan and groan at the same time.

“Aw, fuck! You two are gonna fucking kill me.”

Dean chuckles under his breath and slowly eases out, teasing his cock against the boy’s rim while Cas rides him hard, putting his hands on his chest as he pinches down on his nipples. Dean feels him push down and leans forward, plunging his tongue inside.

“Son of a bitch I taste good as fuck,” Dean moans as his tongue plunges in deeper. “And not because of the cherry lube either.”

Twink!Dean is writhing around on the bed as Dean slides his finger in under his tongue and presses down on his prostate. Dean feels fingers in his hair, judging from how rough they are tugging it isn’t Cas because no matter how into it Cas gets he never is rough unless Dean begs him to be and even then he has to convince Cas he really wants it. He darts his tongue around for a few more minutes then pulls back and kneels on the bed, there are way too many hot noises going on to hold back and he’s not about to miss out on actually fucking his tight perfect ass with more than his tongue.

Dean leans over Cas, sucking down on his neck as he slowly runs his hands up and down his back. He can tell his younger version is so fucked out he can barely form a coherent sentence because even though Dean had been having sex for years by the time he was nineteen he had never had sex as intense as sex with Cas is, it has always been the most pleasure and ecstasy filled experience ever.  He chuckles as he glances down at his pupil blown eyes and feels Cas jerk his face over.

Cas kisses Dean fiercely, snapping his hips hard as Dean reaches around him and wraps his fingers around Cas’s cock, jerking his fist up and down faster until he is moving it in time with his thrusts. He can feel the teenager tightening down on him like a vice. Dean leans forward and starts sucking down on Cas’s neck. Cas gasps as Twink!Dean shoves Dean’s hand off of his dick and the teenager starts sucking down, his tongue swirling around as Cas pulls himself up and slams down, causing him to moan, sending a vibration of pleasure across Cas’s cock. Dean starts thrusting as hard and fast as he can, the bed creaking and moaning from all three of them thrusting, humping and grinding into each other as they all start coming within seconds of each other.

Dean thrusts in franticly as he rides out his orgasm, loving the feeling of his tight ass clamping down on his cock. He also loves not only hearing Cas come apart but also himself as they all climax hard. Dean feels Cas shift and get off of the bed and eases out. The teenager is lying on the bed, completely fucked out.

Cas leans in and whispers to Dean, “We should go, he is in such an altered state right now I can easily wipe his memory and return everything to normal without a fight.”

“But it’s just getting good.”

“I want to go before he is fully conscious. I know you and when you want something you have this way of making me give in and I really don’t want to argue with two of you.”

“We gotta clean him up first. We could all take a shower together.”

Dean grins but can tell Cas is not in the mood, he looks just as fucked out and knows he probably wants to get back to their own time before they start messing around again and Cas gets to the point he can no longer bring them back. Since the teenager’s eyes are closed, Cas puts a hand on both Deans and instantly they are free of the sticky remains of lube, jizz and sweat. Twink!Dean opens his eyes and grins.

“Son of a bitch that was so fucking awesome. I’ve never blacked out from sex before. Fucking incredible. How long was I out?”

Dean glances at Cas and smirks. “You were pretty fucked out in the shower.”

“We messed around in there? _Fuck_ , never felt so damn incredible in my life guess I was in like, a coma from all the awesome sex. So you guys gonna hang out the rest of the week? Still have three days until Sammy gets back.”

Dean shoots Cas a pleading look but he gives Dean his stern extra serious look and Dean knows he better not piss him off or he won’t be as open to sexual things when they get back to the bunker.

“Dude, I’d love to stay. Hell, I’d love to take you with me but it could fuck things up in the future. Besides, the next couple of days are gonna be awesome. Nothing like this…but just enjoy being on your own for a couple days.”

Twink!Dean is trying to figure out ways to get them to stay but knows he will never be able to outwit his older self so he sighs and nods. He sits up and jerks Cas over, kissing him fiercely as he reaches out and puts a hand on Dean’s hip and jerks him closer. He pulls away from Cas and grins.

“See ya in a couple of years, baby. Can’t wait to spend the rest of my life fucking you.”

Dean chuckles as Cas blushes. The teenager sinks down to his knees and teases his lips across the head of Dean’s cock. Dean sucks in a breath and curls his fingers through his hair. When he pushes down the teenager wraps his lips around Dean’s quickly hardening cock and slowly starts to deep throat it.

Dean closes his eyes and groans. “Oh shit! Goddamn our lips feel even better than I imagined. _Fuck!”_

Cas shoots Dean a look and Dean jerks his head over and kisses him, moaning into his mouth as he feels the teenager’s throat stretching out around him.

“Fuck Cas, you know how good it feels to get head from me...just one more minute.”

“Dean, you’re never going to want to leave. We already stayed longer than you promised.”

“Fiiine.” Dean whines, reluctantly pulling out then thrusting in to the incredible tight heat a few more times. When he feels Twink!Dean’s lips tease across his length Dean grunts. “Son of a fucking bitch our lips are fucking awesome.”

As soon as Dean and Cas are dressed again, Cas walks over to the teenager and pushes him down on the bed, kissing him heatedly as he lies over him. Just as the boy closes his eyes Cas puts two fingers on his head and puts him into a deep sleep, erasing his memory of the day.

Dean sighs when Cas gets up and takes his hand. “Damn, sucks to leave. But really I would much rather have you to myself…I mean, just me not me and another me.”

Cas leans in and kisses Dean. They are enveloped in a bright white light and when Dean opens his eyes they are back at the bunker on Dean’s bed. Cas is lying on his side facing him, his fingers slowly carding through Dean’s hair as he watches him.

“Dean, I know you thoroughly enjoyed that, I did too but you do understand that we cannot risk doing it again.”

“Yeah I know. I’ve got enough spank bank material for the rest of my life.” When Cas raises an eyebrow Dean grins. “Not that I would ever have to jerk off again now that I have you.”

“I enjoyed it too. Which is why I figured since you can’t experience it again you should have this.”

Cas hands Dean a memory card and Dean sits up so fast he almost snaps his neck. “You recorded it? Goddamn I love you.”

“I’ve heard enough blasphemy for the day from the younger version of you, quit saying it.”

“Why don’t you make me?” Dean kisses Cas and grins. “Sorry, guess that little shit rubbed off on me.”

Dean grabs his laptop and opens it, sliding the card into the slot. He pulls Cas so he is lying on his chest and jerks his head up and kisses him. “Better lose the clothes. I have a feeling I’m not going to want to mess with them here in a few seconds.”

In the blink of an eye both of their clothes are in a pile on the floor. Dean grins. “Love when you do that. You’ve gotta admit your powers do come in handy when it comes to having sex.”

Cas presses several buttons on the laptop until the recording starts but Dean quickly hits pause.

“So tomorrow after we put the mirrors on the ceilings we can do anything you want.”

He leans in and kisses Cas, his tongue ravaging wildly around his mouth as he moves the laptop and pushes Cas onto his back as he nudges his legs apart and lies above him.

Just as Cas is getting into the kiss, Dean pulls back and a devilishly seductive grin crosses his face. Cas gulps because he knows that grin, Dean uses it when he wants Cas to give in to one of his fantasies.

“You know, I was thinking…”

_“NO.”_

“What? You haven’t even heard what I was going to say.”

“I don’t have to, I know that look. No more crazy insane fantasies.”

Dean teases his cock just barely into Cas and kisses him as he pulls back. “Aw c’mon baby, you know you love my kinky fantasies.”

“Not if it involves time travel.”

“It doesn’t.”

Cas raises an eyebrow and Dean rolls his eyes. “Well not really…”

“Dean...”

“Remember back when we were worried about the Apocalypse?”

Cas’s eyebrows mash together as he squints his eyes. “Of course. What does it have to do with anything?”

“Well, Zachariah sent me to this future vision thing…like an alternate reality.”

“Are you suggesting that I make an alternate reality to recreate today?”

“No. Wait, you could do that?”

“Just get to your point.”

“There was this really crazy hot version of you and he was sexual and liked orgies and _fuck_ , can you imagine if we went and had a threesome with him?”

Cas’s eyes grew huge. “Do you know the amount of power that would require? Just traveling back took enormous amounts, but to produce something like that…whatever happened to mirrors and sex swings? Now your fantasies are going to involve spells and use of my powers? What next? An orgy with several versions of you and I?”

Dean smirked and kissed Cas. “So you agree to the sex swing?”

“If it means no more of these insane fantasies.”

“Mirrors too?”

Dean smiles as Cas rolls his eyes and nods.

“Plus I get to tie you up after we make a little field trip.”

“Field trip where?”

Dean smirks and reaches into the drawer in the bedside table. He slaps a pair of handcuffs onto Cas then pulls a blindfold over his eyes. Just as Cas is about to object, he feels Dean pulling clothes onto him. He feels something incredibly silky against his cock and immediately blushes.

“Dean! Those better not be what I think they are.”

Dean pulls Cas off the bed and kisses him as he tugs on the thong so it pulls tightly against Cas’s quickly hardening cock.

“You know you love ‘em. Look at you soaking your pretty little panties. I knew I’d get you to agree to wear them.”

Cas sighs then moans softly when he feels Dean pressing tightly against them. “Just promise no more time travel or spells or anything like that.”

“I promise. Now I’m gonna need you to zap us somewhere but that doesn’t count as things we can’t do with your powers.”

As soon as Cas sees what Dean is thinking he quickly puts two fingers to Dean’s forehead and they are instantly zapped to Dean’s latest fantasy. Cas doesn’t even mind that Dean is slowly getting him to give in to every fantasy he has ever had because they get hotter and kinkier every time and he can hardly wait to see what Dean will come up with after this one.

 


End file.
